WO1999034775A1

WO1999034775A1 - Use of silicones with ester functions as anti-transfer agents in cosmetic compositions

Info

Publication number: WO1999034775A1
Application number: PCT/FR1998/002898
Authority: WO
Inventors: Jean-Marc Ricca
Original assignee: Rhodia Chimie
Priority date: 1997-12-30
Filing date: 1998-12-29
Publication date: 1999-07-15
Also published as: FR2773073A1; AU4119499A; FR2773073B1; EP1043972A1

Abstract

The invention concerns the use of liquid polyorganosiloxanes with ester functions (acetoxyalkyl) as anti-transfer agents in cosmetic compositions, in particular in the form of solar gels, deodorants, antiperspirants, make-up and beauty care products. The invention also concerns a method for providing anti-transfer properties to cosmetic products by adding to said compositions of at least one liquid polyorganosiloxane with ester functions (acetoxyalkyl). The invention further concerns cosmetic compositions, particularly in the form of solar gels, deodorants, antiperspirants, make-up and beauty care products, comprising at least one liquid polyorganosiloxane with ester functions (acetoxyalkyl).

Description

USE OF SILICONES WITH ESTER FUNCTIONS AS ANTI-TRANSFER AGENTS IN COSMETIC COMPOSITIONS

The present invention relates to the use of liquid organopoiysiloxanes (silicones) with ester functions (acetoxyalkyls) as anti-transfer agents in cosmetic compositions. It also relates to a process for providing anti-transfer properties to cosmetic compositions by adding to said compositions at least one liquid polyorganosiloxane with ester functions (acetoxyalkyls), as well as cosmetic compositions, in particular in the form of sun gels, deodorants. , antiperspirants, make-up or care products, comprising said liquid polyorganosiloxane with ester functions (acetoxyalkyls).

In many cosmetic compositions such as makeup, deodorant, antiperspirant, sun protection, or care products, a recurring problem concerns transfer by contact with the skin or other surfaces such as glass, metals, fabrics , of all or part of the formulation, transfer often resulting in the formation of spots. This phenomenon also encourages repeated applications of product following transfer losses. Many silicones are used today to improve these antitransfer properties in particular in applications of the lipstick, mascara, and foundation type. On the other hand, these formulations have the disadvantage of having a drier sensory profile than the traditional formulations.

The Applicant has found that liquid polyorganosiloxanes comprising acetoxyalkyl functions in which the alkyl group contains at least 3 carbon atoms, were very particularly advantageous for imparting anti-transfer properties to certain cosmetic compositions, in particular to make-up formulations, while providing a sensory profile closely resembling that of conventional non-transfer formulations.

A first subject of the invention therefore consists in the use as anti-transfer agents, in cosmetic compositions, of polyorganosiloxanes with ester functions of formula (I) below:

R ¹ R2 R3 Si O (R ⁴ R ⁵ Si O) _p (R ⁶ Q Si O) _q Si R ³ R ² R ¹ (I) where

- the symbols R ¹ , R ² are identical or different and represent. a C- alkyl radical | with Cg or phenyl, preferably methyl

. or a group -OR ⁷ , where R ⁷ represents a linear or branched C- alkyl radical _| to Cg, preferably methyl the symbols R ⁴ , R ^ and R> are identical or different and represent a C 1 to C 6 alkyl or phenyl radical, preferably methyl,

- the identical or different symbols R ³ represent

. a linear or branched C- alkyl radical | with Cg or phenyl, preferably methyl

. the Q symbol

. or a group -OR ⁷ , where R ⁷ represents a linear or branched C1 to C4 alkyl radical, preferably methyl

- the identical or different symbols Q, represent an ester function or an alcohol function, of formulas (1) and (2) respectively

- R'OCOR "(1) -R'OH (2) where

. R 'represents a linear or branched C3 - C20 alkylene group. preferably in C3 - C-j 2. very particularly trimethylene or 2-methyl trimethylene,. R "represents a methyl group, at least one of the symbols Q representing an ester function of formula (1)

- β represents an average number greater than or equal to 0, preferably ranging from 5 to 100,

- a represents an average number greater than or equal to 0, preferably ranging from 1 to 50, very particularly ranging from 1 to 30, at least one of the symbols R ³ representing the symbol Q ester of formula (1) when a is equal to 0, said polyorganosiloxanes having ester functions being in liquid form under normal conditions of temperature and pressure.

A second subject of the invention consists in a process for providing anti-transfer properties to cosmetic compositions by adding to said compositions at least one polyorganosiloxane with ester functions of formula (I), said polyorganosiloxane with ester functions being present in liquid form under normal conditions of temperature and pressure.

A third subject of the invention consists of cosmetic compositions comprising at least one polyorganosiloxane with ester functions of formula (I), said polyorganosiloxane with ester functions being in liquid form under normal conditions of temperature and pressure.

Among the preferred polyorganosiloxanes with ester functions of formula (I), mention may be made of those with acetoxyalkyl functions of formulas (II), (III) and (IV) below, (II) very particularly e ₃ Si O (SiMe ₂ O) _p > (SiMeQO) _q . SiMe ₃ (II)

Me ₂ Q Si O (SiMe O) _p . (SiMeQO) _q 'Si Q Me ₂ (III)

Me ₂ Q Si O (SiMe ₂ O) _p "Si Q Me ₂ (IV) formulas in which: . Me represents the methyl radical

. β | represents an average number of the order of 0 to 500, preferably of the order of 5 to

100

. β! represents an average number of the order of 0 to 100, preferably of the order of 0 to 20

. al represents an average number of the order of 1 to 50, preferably of the order of 1 to

30

. Q represents an acetoxyalkyl function of formula - ROCOCH3 or an alcohol function -R'OH, where R 'represents a trimethylene or 2-methyltrimethylene group, very particularly trimethylene, at least one of the symbols Q representing an acetoxyalkyl function - ROCOCH3. Preferably, all the symbols Q represent an ester function. Said polyorganosiloxanes containing ester functions of formula (I) can be obtained by * hydrosilylation between a hydrogenopolyorganosiloxane oil of formula (V)

R ¹ R ² R ³ 'Si O (R ⁴ R ⁵ Si O) _p (R ⁶ H Si O) _q Si R ³ ' R ² R ¹ (V) where:

- the symbols R ¹ , R ² _< R ⁴ , R ^, R6, Q and a have the definition given above

- the identical or different symbols R ³ 'represent. a linear or branched C- alkyl radical | to Cg or phenyl, preferably methyl. H

. or a group -OR ⁷ , in which R ⁷ represents a linear or branched C 1 to C 8 alkyl radical, preferably methyl and an olefinic alcohol of formula ROH, formula in which R represents an olefinic radical from which the bivalent radical R 'is derived by opening the double bond in α and adding hydrogen, preferably an allyl or methallyl radical, * then esterification of the hydroxyalkylated polyorganosiloxane of formula (VI) obtained

R ¹ R ² R ³ "Si O (R ⁴ R ⁵ Si O) _p (R ⁶ Q 'Si O) _q Si R ³ " R ² R ¹ (VI) where:

- the symbols R ¹ , R ² , R ⁴ ,, R6, Q and a have the definition given above

- the identical or different symbols R ³ "represent

. a linear or branched C- alkyl radical | to Cg or phenyl, preferably methyl. the symbol Q '

. or a group -OR ⁷ , where R ⁷ has the definition given above

- the symbol Q 'represents the radical -R'OH, where R' has the definition given above, by an acyl halide of formula XCOR ", where R" has the definition given above_and

X represents a halogen atom, notably chlorine.

* and elimination of the olefinic by-products and of the hydrohalic acid formed.

The hydrosilylation step can be carried out in a well known manner at a temperature of the order of 20 ° C to 200 ° C, preferably of the order of 60 ° C to 120 ° C, in the presence of a hydrosilylation catalyst, in particular based on platinum.

The relative amounts of hydrogenopolyorganosiloxane of formula (V) and α olefinic alcohol ROH, generally correspond to a molar ratio α olefinic alcohol / hydrogenopolyorganosiloxane greater than 1 and less than or equal to 5, preferably greater than 1 and less than or equal to 2.

In the definition of the mole of α olefinic alcohol, we will consider as elementary entity the olefinic unsaturation; in the definition of the mole of hydrogenopolyorganosiloxane, we will consider as elementary entity the function

SiH. The operation is carried out until the -SiH groups disappear in the reaction mass.

Excess olefinic alcohol can be removed by vacuum distillation.

The hydrogenopolyorganosiloxane used in the hydrosilylation step is preferably chosen from those of formulas: Me ₃ Si O (SiMe ₂ O) _p - (SiMeHO) _q - SiMe ₃

Me ₂ H Si O (SiMe O) _p - (SiMeHO) _q - Si H Me ₂ Me ₂ H Si O (SiMe ₂ O) _p "Si H Me formulas in which:. Me represents the methyl radical. β! represents an average number of the order of 0 to 500, preferably of the order of 5 to 100

. if represents an average number of the order of 1 to 50, preferably of the order of 1 to 30.

The α olefinic alcohol of formula ROH used in the hydrosilylation stage is preferably allylic or methallylic alcohol.

The esterification operation can be carried out at a temperature of the order of 0 ° C to 100 ° C, preferably of the order of 25 ° C to 50 ° C, in the absence or in the presence of a esterification catalyst.

The relative amounts of hydroxyalkylated polyorganosiloxane and of acyl halide of formula XCOR "generally correspond to a molar ratio of acyl halide / hydroxy-alkylated polyorganosiloxane of the order of 0.1 to 2, preferably of the order of 0.1 to 1.

In the definition of the mole of hydroxy-alkylated polyorganosiloxane, the hydroxy-alkyl function will be considered as elementary entity. The acyl halide of formula XCOR "most particularly used in the esterification step is acetyl chloride.

The acid halide formed by esterification can be removed by entrainment using an inert gas, then by treatment with a base. After devolatization of the by-products, the polyorganosiloxane having an ester function can then be recovered by filtration, for example.

This process has the advantage of leading to polyorganosiloxanes with ester functions, of very high purity, that is to say products in which the overall contents of olefinic siloxane units and / or olefinic impurities, with undesirable effects. or capable of reacting, correspond to a number of α olefinic groups per 100 g of polyorganosiloxane with ester function obtained less than 10 ⁻³ , preferably less than ^{5 × 1} O ^{* 4} .

The α olefinic siloxane units and α olefinic impurities are those of formulas - Si - O - R, ROH and R "COOR, where R represents an α olefinic radical, linear or branched, having 3 to 20 carbon atoms, as defined above (allyl or methallyl for example).

The polyorganosiloxanes with ester functions of formula (I) are present in the liquid state under normal conditions of temperature and pressure, that is to say at a temperature of the order of 10 to 30 ° C under atmospheric pressure . They have viscosities generally less than 5000 mPa.s. The term cosmetic composition or formulation means all cosmetic products or preparations such as those described in Annex I ("illustrative list by category of cosmetic products") of European Directive No. 76/768 / EEC of July 27, 1976, so-called cosmetic directive.

For good use as anti-transfer agents in cosmetic compositions, said polyorganosiloxanes with ester functions of the above formulas can be used at a rate of 0.1% to 30%, preferably from 3% to 10% by weight said cosmetic compositions.

The cosmetic compositions containing said polyorganosiloxanes with ester functions of the above formulas as anti-transfer agents, can be formulated in a large number of types of products for the skin and / or the hair (or more generally keratin), such as foams. , gels (especially styling), conditioners, formulations for styling or to facilitate combing of hair, rinsing formulas, hand and body lotions, products regulating the hydration of the skin, toilet milks, makeup-removing compositions, creams or lotions for protection against the sun and ultraviolet radiation, care creams, anti-acne preparations, local analgesics, mascaras, deodorants , antiperspirants, lipsticks and many other compositions of the same type.

Preferably, said polyorganosiloxanes having ester functions are used in cosmetic anti-transfer compositions for the skin.

Said cosmetic compositions may use a vehicle or a mixture of vehicles compatible with application to the hair and / or the skin. Said vehicle can represent from 0.5% to 99.5% approximately of the weight of said composition, preferably from 5 to 90% approximately. The term "compatible with an application on the hair and / or the skin" means here that the other vehicle does not damage or exert any negative effects on the appearance of the hair and / or the skin or does not create no skin and / or eye and / or scalp irritation. The vehicles compatible with the applications described in this invention include those usually used in cosmetic compositions for the hair and / or the skin, for example those present in sprays, mousses, tonics, gels, shampoos, or lotions rinse. The choice of the appropriate vehicle will depend on the nature of the ingredients used, and the destination of the formulated product, depending on whether it is supposed to be left on the surface where it has been applied (e.g. sprays, foams, tonic lotion, cream, or gels) or rinsed off after use (e.g. shampoo, conditioner, rinse lotions). Said vehicles can consist of at least one solvent to dissolve or disperse the ingredients used, such as water, Cf-Cg alcohols, and their mixtures (in particular water and methanol, ethanol, isopropanol, and mixtures thereof), or other solvents such as acetone, hydrocarbons (such as isobutane, hexane, decane), halogenated hydrocarbons (such as freons), linalool, esters (such as acetate, dibutyl phthalate), volatile silicones (in particular phenyl pentamethyl siloxane, methoxypropyl heptamethyl cyclotetrasiloxane, chloropropyl pentamethyldisiloxane, hydroxypropyl pentamethyl disiloxane, octamethyl cyclotetrasiloxane, decamethyl cycloxane hexamethyl disiloxane, octamethyltrisiloxane, decamethyltetrasiloxane) and their mixtures. All of the vehicles used can consist of solvents which are miscible or immiscible with each other. When the cosmetic compositions are in the form of sprays, tonic lotions, gels, or foams, the preferred preferential solvents include water, ethanol, volatile silicones and their mixtures. Foams and aerosol sprays can also use any propellant capable of generating the products in the form of foam or in the form of fine, uniform sprays. By way of examples, mention may be made of trichlorofluoromethane, dichlorodifluoromethane, difluoroethane, dimethyl ether, propane, n-butane, or isobutane.

The polyorganosiloxanes with ester function of formula (I) are particularly well suited for uses as anti-transfer agents in cosmetic compositions containing at least 3%, preferably from 5 to 90% of alcoholic solvents such as ethanol, propylene glycol , glycerol. Vehicles can take many forms, for example, the form of emulsions including water in oil, oil in water emulsions, and multiple emulsions. These emulsions cover a wide viscosity range, from 100 to 2,000,000 mPa.s. . These emulsions can also be delivered in the form of foams or sprays using either a device of the mechanical pump type, or in the form of an aerosol pressurized by the use of a propellant gas. They can also be rheologically modified (increase in viscosity) for example by the addition of gums, resins, polymers, waxes or salts.

In addition to said ester-functional polyorganosiloxanes of formula (I), at least 0.5% of at least one cosmetically acceptable ingredient may be present in said cosmetic compositions.

Thus, said compositions can comprise at least one surfactant. The polyorganosiloxanes having an ester function of formula (I) can be present in said compositions in the form of dispersed particles of size which can range from 0.02 to 100 microns (emulsions), or in the form of microemulsions. Said cosmetic compositions can comprise:

- of the order of 1 to 60% of their weight, preferably of the order of 5 to 25% of their weight, of at least one surfactant

- Of the order of 0.5 to 50% of their weight, preferably of the order of 0.5 to 10% of their weight, of at least one polyorganosiloxane with ester function of formula (I). Said surfactants are used to disperse, emulsify, dissolve and stabilize the various constituents of the composition, in particular those used for their anti-transfer, emollient or humectant properties.

The surfactants which may be present in said cosmetic compositions may be of the anionic, nonionic, cationic, zwitterionic or amphoteric type; examples that may be mentioned include anionic surfactants such as

. alkyl sulfonate esters of formula R-CH (Sθ3M) -COOR ', where R represents a C8-C ₂ o alkyl radical. preferably in Cio-C-ig, R 'an alkyl radical in Cj-Cg, of preferably in C- | -C3 and M an alkali cation (sodium, potassium, lithium), substituted or unsubstituted ammonium (methyl-, dimethyl-, trimethyl-, tetramethylammonium, dimethylpiperidinium ...) or derived from an alkanolamine (monoethanolamine , diethanolamine, triethanolamine ...). Mention may very particularly be made of methyl ester sulfonates whose radicals R is C 1 -C 4 g;

. alkyl sulphates of formula ROSO3M, where R represents a C-jo-C ₂ 4, preferably C-, alkyl or hydroxyalkyl radical | ₂ -C ₂ o and especially in C- | ₂ - C- | 8 _> M representing a hydrogen atom or a cation of the same definition as above, as well as their ethoxylenated (OE) and / or propoxylenated (OP) derivatives, having on average from 0.5 to 6 units, preferably from 0.5 to 3 OE units and / or OP units;

. the sulfonated alkylamides of formula RCONHROSO3M where R represents a C ₂ -C ₂₂ , preferably C ₁ -C ₂₂ alkyl radical, R 'a C -C 3 alkyl radical, M representing a hydrogen atom or a cation of the same definition as above, as well as their ethoxylenated (OE) and / or propoxylenated (OP) derivatives, having on average from 0.5 to 60 OE and / or OP units;

. salts of C8-C 4, preferably C-) 4-C ₂ rj saturated or unsaturated fatty acids, Cg-C ₂ o alkylbenzenesulfonates. primary or secondary C ₆ -C ₂₂ alkyl sulfonates. 'es alkylglycerol sulfonates, sulfonated polycarboxylic acids described in GB-A-1 082 179, paraffin sulfonates, N-acyl N-alkyltaurates, alkylphosphates, alkylisethionates, alkylsuccinamates, alkylsulfosuccinates, monoesters or diesters of sulfosuccinates, N-acyl sarcosinates, alkyl glycoside sulfates, polyethoxycarboxylates, the cation being an alkali metal (sodium, potassium, lithium), a substituted or unsubstituted ammonium residue (methyl-, dimethyl-, trimethyl-, tetramethylammonium, dimethylpiperidinium, etc.). .) or derived from an alkanolamine (monoethanolamine, diethanolamine, triethanolamine ...); non-ionic surfactants such as: polyoxyalkylenated (polyethoxyethylenated, polyoxypropylenated, polyoxybutylenated) alkylphenols in which the alkyl substituent is Cg-C- | ₂ and containing from 5 to 25 oxyalkylene units; by way of example, mention may be made of the Triton X-45, X-114, X-100 or X-102 sold by Rohm & Haas Cy. ; . glucosamides, glucamides;

. glycerolamides derived from N-alkylamines (US-A-5,223,179 and FR-A-1,585,966). polyoxyalkylenated Cg-C ₂₂ aliphatic alcohols containing from 1 to 25 oxyalkylene units (oxyethylene, oxypropylene); by way of example, mention may be made of TERGITOL 15-S-9, TERGITOL 24-L-6 NMW sold by Union Carbide Corp., NEODOL 45-9, NEODOL 23-65, NEODOL 45-7, NEODOL 45-4 marketed by Shell Chemical Cy., KYRO EOB marketed by The Procter & Gamble Co. . the products resulting from the condensation of ethylene oxide with a hydrophobic compound resulting from the condensation of propylene oxide with propylene glycol, such as the Pluronic sold by BASF;

. amine oxides such as Cig-Ci g dimethylamine oxides, Cg-C2 ₂ alkoxy ethyl dihydroxy ethylamines;

. the alkylpolyglycosides described in US-A-4,565,647 and their polyoxyalkylenated derivatives; . fatty acid amides of Cg-C ₂ o. ethoxylated fatty acids. amides, amines, ethoxylated amidoamines amphoteric and zwitterionic surfactants such as

* those of betaine type like

• betaines

R1 R2 R3 R4 C (0) 0 "

sulfo-betaines

R1 R2 R3 ⁺ NR4 SO ₃ "amidoalkylbetaines

R1C (O) - NH R2N (R3 R4) R5 C (O) O "

* and sulfo-betaines

R1C (O) - NH R2N (R3 R4) R5 SO3- formulas in which the radicals R ¹ represents an alkyl or alkenyl radical of 10 to 24 carbon atoms, R2, R3, R4, and R5 identical or different represent an alkyl radical or aikylene having from 1 to 4 carbon atoms.

* condensation products of fatty acids and protein hydrolysates,

* cocoamphoacetates and cocoamphodiacetates more generally corresponding to the formula

R1C (0) - NH - CH ₂ CH ₂ -N - CH2CH2 - OH

I CH ₂ C (O) O Na in which R1 has the above meaning and most often represents coconut and lauryl chains.

* alkylamphopropionates or -dipropionates,

* amphoteric derivatives of alkyl polyamines such as AMPHIONIC XL® marketed by RHONE-POULENC, AMPHOLAC 7T / X® and AMPHOLAC 7C / X® marketed by AKZO NOBEL. The polyorganosiloxanes having an ester function of formula (I) also have a good affinity for surfaces, and, by their silicone character, contribute to the apparent modification of these surfaces, this being able to result in the case of the hair by more combability. easy on wet hair or an increase in shine or volume, and in the case of the skin by a sensory signal.

Said cosmetic compositions in which the polyorganosiloxanes having an ester function of formula (I) are used can therefore also contain non-water-soluble and non-volatile organopolysiloxanes (also called hereinafter "non-water-soluble and non-volatile silicones"). Among these, mention may be made of polyalkylsiloxane, polyarylsiioxane, polyalkylarylsiloxane oils, gums or resins, or their non-water-soluble functionalized derivatives, or their non-volatile mixtures. Said organopolysiloxanes are considered to be non-water-soluble and non-volatile when their solubility in water is less than 50 grams / liter and their intrinsic viscosity is at least 300 mPa.s. at 25 ° C. As examples of non-water-soluble and non-volatile organopolysiloxanes or silicones, mention may be made of silicone gums such as, for example, diphenyl dimethicone gum sold by the company Rhône-Poulenc, and preferably polydimethylsiloxanes having a viscosity at least equal to 60,000 mPa.s. at 25 ° C, and even more preferably, those with a viscosity greater than 2,000,000 mPa.s. at 25 ° C, such as the Mirasil DM 500000® sold by the company Rhône-Poulenc.

The cosmetic compositions in which the polyorganosiloxanes having an ester function of formula (I) are used, may also contain conditioning agents. Among the conditioning agents which can be used in the context of this invention, there are conditioning agents of animal origin, such as hydrolysates of animal proteins, such as the ammonium salt of dimethyl- or trimethyl stearate of collagen hydrolysates, silk, keratin; conditioning agents of synthetic origin, better known under the name polyquaternium, such as the copolymer of N, N'-bis ((dimethylamino) -3 propyl) urea and oxy-1,1 'bis (chloro-2) ethane or polyquaternium-2, the copolymer of diallyidimethyl ammonium chloride and acrylamide or polyquaternium-7; cationic derivatives of polysaccharides, such as cocodimonium hydroxyethyl cellulose, guar hydroxypropyl trimonium chloride, hydroxypropyl guar hydroxypropyl trimonium chloride (JAGUAR C13S®, JAGUAR C162® sold by RHONE-POULENC), poly (oxyethanediyl-1 ether, 2) 2-hydroxy-3-trimethylammonium chloride propyl cellulose or polyquaternium-10; silicone derivatives such as amodimethicone, cetoly dimethicone copolyol, dimethicone copolyol, trimethylsilyl amodimethicone, polyquaternium-80; cationic surfactants such as polyalkyl ammonium halides for example distearyl dimethyl ammonium chloride or behenyl trimonium chloride.

Conditioners are preferably chosen from conditioners of synthetic origin, in particular polyquaterniums -2, -7, and -10, and cationic derivatives of polysaccharides, such as cocodimonium hydroxyethyl cellulose, guar hydroxypropyl trimonium chloride, l 'hydroxypropyl guar hydroxypropyl trimonium chloride.

It is preferable to use the cationic derivatives of polysaccharides, and in particular the guar derivatives such as guar hydroxypropyl trimonium chloride and hydroxypropyl guar hydroxypropyl trimonium chloride.

The anti-transfer cosmetic compositions in which the polyorganosiloxanes having an ester function of formula (I) are used, may also contain polymers with film-forming properties which can also be used as fixing resins. These polymers with film-forming properties are generally present in said compositions at concentrations of between 0.01 and 10%, preferably between 0.5 and 5%.

The polymers with film-forming properties are preferably chosen from the following oligomers, polymers, copolymers or resins: * methyl acrylate / acrylamide copolymers, polyvinylmethylether / maleic anhydride copolymers, vinyl acetate / crotonic acid copolymers, octylacrylamide / methyl acrylate / butylaminoethylmethacrylate copolymers, polyvinylpyrrolidones, polyvinylpyrrolidone / methyl methacrylate copolymers, polyvinylpyrrolidone / vinyl acetate copolymers, polyvinyl alcohols, polyvinyl alcohol / crotonic acid copolymers, polyvinyl alcohol / maleic anhydride copolymers, hydroxypropyl celluloses, hydroxypropyl guyrones, hydroxyalkyl polypropylene guards, hydroxyalkyl hydroxypropyl guars / ethyl methacrylate / methacrylic acid, monomethyl ethers of poly (methylvinyl ether / maleic acid), polyvinylacetates grafted onto polyoxyethylene trunks ( EP-A-219 048), * copolyesters derived from acid, anhydride or from a terephthalic and / or isophthalic and / or sulfoisophthalic diester and from a diol, such as

. polyester copolymers based on ethylene terephthalate and / or propylene terephthalate and polyoxyethylene terephthalate units, (US-A-3,959,230, US-A-3,893,929, US-A-4,116,896, US-A-4,702,857, US-A-4770666); . sulfonated polyester oligomers obtained by sulfonation of an oligomer derived from ethoxylated allyl alcohol, dimethyl terephthalate and 1,2 propylene diol (US-A-4968451) . polyester copolymers based on propylene terephthalate and polyoxyethylene terephthalate units and terminated by ethyl or methyl units (US-A-4,711,730) or polyester oligomers terminated by alkylpolyethoxy groups (US-A-4,702,857) or groups anionic sulfopolyethoxy (US-A-4,721,580), sulfoaroyl (US-A-4877 896)

. the polyester polyurethanes obtained by reaction of a polyester obtained from adipic acid and / or terephthalic acid and / or sulfoisophthalic acid and a diol, on a prepolymer with terminal isocyanate groups obtained from a polyoxyethylene glycol and a diisocyanate (FR-A-2334698). ethoxylated onoamines or polyamines, ethoxylated amine polymers (US-A-4597898, EP-A-11 984)

. the sulfonated polyester oligomers obtained by condensation of isophthalic acid, of dimethyl sulfosuccinate and of diethylene glycol (FR-A-2236 926). polyester copolymers derived from dimethyl terephthalate, isophthalic acid, dimethyl sulfoisophthalate and ethylene glycol (EP-A-540374)

. copolymers comprising polyester units derived from dimethyl terephthalate, isophthalic acid, dimethyl sulfoisophthalate and ethylene glycol and polyorganosiloxane units (FR-A-2728915). * cationic resins derived in whole or in part from cationic monomers such as, for example, dimethylaminoethyl methacrylate, quaternized dimethylaminoethyl methacrylate, diallyldimethyl ammonium chloride, or mixtures thereof.

Preferably, the film-forming polymers are of the polyvinylpyrrolidone (PVP) type, polyvinylpyrrolidone and methyl methacrylate copolymers, polyvinylpyrrolidone and vinyl acetate (VA) copolymer, polyterephthalic ethylene glycol / polyethylene glycol copolymers, polyterephthalate copolymers. ethylene glycol / polyethylene glycol / sodium polyisophthalate sulfonate, and mixtures thereof. These film-forming polymers are preferably dispersed or dissolved in the chosen vehicle.

The anti-transfer cosmetic compositions in which the polyorganosiloxanes having an ester function of formula (I) are used, may also contain polymeric derivatives exerting a protective function. These polymer derivatives can be present in said compositions in amounts of the order of 0.01-10%, preferably about 0.1-5%, and very particularly of the order of 0.2-3% by weight, agents such as:

. cellulose derivatives such as cellulose hydroxyethers, methylcellulose, ethylcellulose, hydroxypropyl methylcellulose, hydroxybutyl methylcellulose. . polyvinyl esters grafted on polyalkylene trunks such as polyvinyl acetates grafted on polyoxyethylene trunks (EP-A-219048). polyvinyl alcohols

. copolyesters derived from acid, anhydride or a terephthalic and / or isophthalic and / or sulfoisophthalic diester and a diol described above

. ethoxylated monoamines or polyamines, ethoxylated amine polymers (US-A-4,597,898, EP-A-11,984).

The performance of said cosmetic compositions can also be improved by the use of plasticizing agents. These constitute from 0.1 to 20% of the formulation, preferably from 1 to 15%. Among the particularly useful plasticizers, there may be mentioned adipates, phthalates, isophthalates, azelates, stearates, silicone copolyols, glycols, castor oil, or mixtures thereof.

One can also advantageously add to these compositions metal sequestering agents, more particularly those sequestering calcium such as citrate ions.

Humectants can also be incorporated into these cosmetic compositions; there may be mentioned glycerol, sorbitol, urea, collagen, gelatin, aloe vera, hyaluronic acid, and emollients which are generally chosen from alkylmonoglycerides, alkyldiglycerides, triglycerides such as oils extracted from plants and plants (palm, copra, cottonseed, soybean, sunflower, olive, grapeseed, sesame, peanut, castor oil, etc.) or animal origin (tallow, fish oils, ...), derivatives of these oils such as hydrogenated oils, lanolin derivatives, mineral oils or paraffinic oils, perhydrosqualane, squalene, diols such as 1 - 2-propanediol, 1 -3-butanediol, cetyl alcohol, stearyl alcohol, oleic alcohol, polyethylene glycols or polypropylene glycols, fatty esters such as isopropyl palmitate, ethyl cocoate-2-hexyl , myristyl myristate, esters of lactic acid, stearic acid, behenic acid, isostearic acid.

To further reduce the irritation or aggression of the skin tissue, it is also possible to add water-soluble or water-dispersible polymers such as collagen or certain non-allergenic derivatives of animal or vegetable proteins (wheat protein hydrolysates for example), natural hydrocolloids ( guar, carob, tara gum) or derived from fermentation processes and derivatives of these polycarbohydrates such as modified celluloses (for example hydroxyethylcellulose, carboxymethylceliulose), guar or carob derivatives such as their cationic derivatives or non-derivatives -ionics (for example hydroxypropylguar), anionic derivatives (carboxymethylguar and carboxymethyl hydroxypropylguar). Specific anti-transfer cosmetic compositions in which the polyorganosiloxanes having an ester function of formula (I) are used as anti-transfer agents, are those comprising an oily medium.

Among these oily media, there may be mentioned, for example, those whose main fatty phase is of the type

- aliphatic fatty alcohols saturated or unsaturated with Cg-C ₂₂ , preferably with C-j4-C ₂ o, optionally containing 1 or more oxygen heteroatoms

- ethers of polyethylene glycol or polypropylene glycol and fatty alcohols in C4-C22, preferably in C10-C20 - acetic esters of aliphatic fatty alcohols saturated or unsaturated in Cg-C ₂₂ , preferably in C- | 4- C ₂ o, possibly containing 1 or more heteroatoms of oxygen

- aliphatic diesters of C ₂ -CI Q dicarboxylic acids, preferably C ₂ -C ₈ - natural or synthetic triglycerides

- aliphatic isoparaffinic oils

- paraffinic oils

- polyisobutenes oils possibly hydrogenated

- mineral oils - low viscosity non-volatile silicone oils

The amount of polyorganosiloxane having an ester function of formula (I) which can be used in said oily media is preferably of the order of 0.2 to 50, preferably of the order of 2 to 10 parts by weight per 100 parts in weight of said oily media. A fatty phase is considered to be the main in an oily medium, when the latter represents of the order of at least 10%, preferably at least 40% by weight of said oily medium.

Among these main fatty phases, there may be mentioned in particular

- oleic alcohol - isopropyl adipate

- polypropylene glycol (PPG) -3 myristyl ether (WITCONOL APM® marketed by WITCO), PPG-4 myristyl ether, PPG-4 lauryl ether, PPG-10 ketyl ether

- mixtures of cetyl acetate and lanolin acetyl alcohol (CRODALAN LA® marketed by CRODA) - caprylic acid triglyceride

- corn oil

- grapeseed oil

- sweet almond oil - jojoba oil

- squalane

- optionally hydrogenated polyisobutenes

- petroleum jelly oil - paraffinic oils such as petroleum jelly oil

- isoparaffinic oils (MARCHOL 52® and MARCHOL 82® marketed by ESSO)

- dimethicones with a viscosity of less than 5000 mPa.s.

- phenyltrimethicone (MIRASIL PTM from Rhône-Poulenc) - diphenyldimethicone with viscosity less than 5000 mPa.s.

Oily media composed of mixtures of cosmetic emollients of the type of those appearing in particular in "Cosmetics & Toiletries" / No. 93, page 107-July 1992, are very particularly preferred.

Said cosmetic composition can be constituted by said oily medium itself, optionally thickened, or by a single or multiple emulsion "water in oil" or "oil in water", emulsion in which the oil phase consists of said oily medium optionally thickened .

Said composition containing said oily medium optionally thickened present as such or in the form of a single or multiple emulsion "water in oil" or "oil in water", may also contain other conventional additives for cosmetic formulations such as for example waxes silicones, non-silicone waxes or mineral derivatives. Said composition can also be a solid formulation which can optionally be shaped by molding, such as, for example, deodorants, antiperspirants or lipsticks. Said ester-functional polyorganosiloxanes of formula (I) are very particularly advantageous for the formulation of oily media used in the composition of sun gels, deodorants, or make-up products. Said oily media then contain more than 10%, preferably more than 50% of their weight of volatile silicone oils, media which can optionally be thickened in order to form translucent gels by using, for example, alkyl grafted silicone waxes such as MIRASIL WAX B from Rhône-Poulenc (behenic ester dimethicone).

Deodorant or antiperspirant-fighting compositions ("antiperspirants") are described in the literature. Such compositions generally contain silicones due to the sensory properties provided by them. The volatile nature of cyclic silicones results in an absence of feeling of cold after deposition on the skin, a non-greasy, non-sticky feel and excellent lubricating behavior. These highly appreciable properties for giving a cosmetically acceptable character to the compositions are transferred to the others constituents of these compositions such as the active constituents associated with silicones. These compositions may also contain other types of silicone such as those known under the names dimethicone copolyol, diphenyl dimethicone, phenyl dimethicone, amodimethicone ... (CTFA dictionary). Many other components are found in deodorant or "antiperspirant" compositions, either active against perspiration or the formation of unpleasant odors, or modifying the physical appearance of the compositions, depending on whether the final composition is in the form of a liquid, gel or solidified medium. Depending on their physical appearance and depending on the degree of gelation chosen, these compositions can be in the form of sticks, extruded gels, ball applicators, creams, etc.

The application to the skin of the gel, of thick or gelled cream or of the solidified medium is made more pleasant when the melting or softening temperature of the gel is close to the temperature of the skin, which results in an effect of slip during application.

Common thickening, gelling or solidifying agents are the lithium, sodium, potassium, aluminum, zirconium, cerium ... salts, stearic, hydroxystearic, behenic, montanic acids, esters of carboxylic or hydroxycarboxylic acids in C14-C30 and glycol, polyglycol, glycerol, polyglycerol, C ₂ -C ₃₀ aliphatic alcohols, C14-C30 ethers of polyethylene glycol or polypropylene glycol, 0-14-030 aliphatic alcohols, alkyl grafted silicone waxes and in particular waxes behenic ester dimethicone type ... There are also among the texturing agents, conventional waxes having melting points between 30 ° C and 150 ° C such as beeswax, spermaceti, camauba wax, paraffin , microcrystalline waxes, ceresin, ozokerite.

The deodorant or antiperspirant compositions also contain hydroxylated compounds such as ethanol, propylene glycol, glycerol.

While volatile silicones are generally compatible with alcohols, the same does not apply to non-volatile silicones, the presence of which is desirable for providing emollience, water resistance, anti-transfer or afterglow. If certain non-volatile silicones, such as for example dimethicone copolyols, can be introduced in a limited quantity into media containing high proportions of alcohols, their negative contribution to the sensory profile of the composition makes their use very limited. Said polyorganosiloxanes having an ester function of formula (I) are particularly advantageous because they have the property of being compatible with media rich in alcohols, without harming the sensory profile of the formulation. In addition, the polyorganosiloxanes having an ester function of formula (I) improve the cosmetic feel of the composition by providing a feel comparable to that of a mineral oil while benefiting from the specific properties of silicones, such as improving the spreading over the skin or non-comedogenicity. Found among the active agents used in the deodorant and / or antiperspirant compositions, astringent agents limiting perspiration, antibacterial agents, absorbent compounds, additives controlling unpleasant odors such as bis (pyridine) -2-2 ' disulfide described in EP-A-483428 or the amino acids described in WO 91/11998 or also undecylenic acid. Among the astringent compounds, there are organic or inorganic salts of aluminum, zirconium, zinc or their mixed salts or their mixtures. These compounds are described or cited in the literature, in particular in the journal Cosmetics & Toiletries, April 1990, pages 35 to 39. Examples of these compounds are aluminum chloride, aluminum and / or zirconium hydrochloride, dihydrochloride aluminum and / or zirconium, aluminum and / or zirconium trihydrochloride, aluminum and / or zirconium tetrachlorhydrate, aluminum and / or zirconium pentachlorhydrate, aluminum sesquichlorhydrate and / or zirconium, aluminum chlorhydrex, aluminum-zirconium chlorhydrex glycine, aluminum and zirconium octachlorhydrate, aluminum sulfate, zinc sulfate, zirconium and aluminum chlorohydroglycinate, Zirconium hydroxychloride, aluminum and zirconium lactate, aluminum and potassium sulphate, aluminum and sodium chlorohydroxylactate, aluminum bromohydrate, zinc sulfocarbonate, aluminum bromide, zinc phenolsulfonate associated with u alminium sulfate. All these astringent compounds can also be encapsulated or protected by film-coating, adsorption, complexation with polymers or by any other suitable technique such as those described in US-A-4624062.

Bactericidal or bacteriostatic compounds can also be added to these deodorant compositions in order to control the proliferation of the microbial flora developing on the body. Among these compounds, mention may be made of chlorhexidine and its derivatives, nisin, trichlosan, trichlorocarban.

The persistence of these compounds on the skin can be improved, if desired, by adding from 0 to 10% by weight of polymers such as polydimethylsiloxanes and high viscosity polydimethyldiphenylsiloxanes, preferably greater than 100,000 mPa.s.

The astringent compounds are generally present at concentrations of 1% to 70% by weight, preferably from 5 to 50% by weight. The compounds controlling the proliferation of the bacterial flora on the skin can be introduced in concentrations of 0.1 to 10%.

In addition to all these compounds, other volatile compounds such as ethanol, isopropanol, and emollients such as those described in the journal Cosmetics & Toiletries, July 1992, Nj 107, pages 93 et seq. compounds such as alkylmonoglycerides, alkyldiglycerides, diols such as 1-2-propane diol, 1-3, butane diol, polyethylene glycols or polypropylene glycols and their C ₂ -C esters | ₂ , liquid fatty esters such as isopropyl palmitate, ethyl-2-hexyl cocoate, myristyl myristate, C ₂ - C-JO esters of isostearic acids or C -Cg hydroxycarboxylic acids, non-volatile silicones such as linear polyalkylsiloxanes, copolyol silicones or copolyethers ..., perfumes, humectants such as glycerol, sorbitol, urea, collagen, aloe vera, hyaluronic acid, alkoxylated sugar derivatives or their esters such as GLUCAM P20® or GLUCAM E20® sold by AMERCHOL, water. When the composition contains agents of marked hydrophilic nature, compatibilizing agents such as anionic, nonionic, cationic or zwitterionic surfactants can be used. Among these surfactants, those comprising a polyorganosiloxane skeleton are preferred.

Said ester-functional polyorganosiloxanes of formula (I) can be used as anti-transfer agents in cosmetic sunscreen compositions. Other silicones may be present.

Cyclic volatile silicones, such as octamethyl cyclotetrasiloxane, are used for their volatility which allows rapid drying of the composition applied to the skin without resulting in a feeling of cold. In addition, they provide the compositions with the desired cosmetic properties by facilitating the spreading of the compositions on the skin and by reducing the oily or oily nature of these compositions, particularly when they are formulated in the form of oil, sun gel or oily continuous phase emulsion. In general, silicones are also used for their good emollient or protective properties for the skin. These properties are described for example in a monograph of PUS Food and Drug Administration (Department of Health and Human Services, Food and Drug Administration, Skin Protectant Drug Products for Over the Counter Human Use, 21 CFR Part 347). The silicones best suited for their emollient properties are polydimethylsiloxanes, silicone copolyols, diphenyidimethicones, phenyltrimethicones, alkylpolysiloxanes, dimethiconols, with viscosities of between 20 and 10,000 mPa.s.

Water resistance is essential to ensure the persistence over time of sun protection or UV protection on the skin. The use of high molecular weight polydimethylsiloxane to ensure better persistence on the skin of anti UV active agents is taught in EP-A-197485. In particular, polydimethylsiloxane with a degree of polymerization greater than 5000 dimethylsiloxy units are substantially resistant to washing. However, optimizing the sensory profile often involves the use of other compounds than silicones, in particular if the dry appearance needs to be modified. To meet the expectations of consumers who demand more and more "oil-free" products, it becomes necessary to develop alternative solutions to mineral oils, in particular non-occlusive products. Mineral oils have this unwanted occlusiveness property.

In addition to these additives, the cosmetic compositions protecting against the effects of UV radiation contain organic molecules acting as UV filters, or mineral particles acting as a physical barrier to UV radiation. These UV filters or adsorbents are well known in the literature; they are for example described in the article in the journal Cosmetics & Toiletries, Vol 102, March 1987, p21 and following. Mention may be made, for example, of UV filters such as para amino benzoates and their derivatives, salicylates, cinnamates, benzophenones, benzylidene camphor, benzotriazoles and their derivatives and in general the filters cited in Annex 7 to European directive 76/768 / EEC. These UV filters can also be grafted onto a polymer chain, in particular onto a polysiloxane chain.

Among the mineral particles, there may be mentioned particles of titanium oxide, zinc oxide or cerium. These mineral oxide particles or nanoparticles are optionally covered on the surface with polymers, organic molecules or other mineral compounds in order to improve their compatibility with the organic phases and reduce their surface reactivity such as photocatalysis. Said ester-functional polyorganosiloxanes of formula (I) can be introduced into the sun protection compositions at concentrations of between 0.5% and 90% by weight of the composition, preferably from 5% to 20% by weight of this composition, in order to improve the feel of these compositions, to facilitate their spreading, to convey ingredients making it possible to increase the persistence of active agents such as anti UV on the skin and to maintain over time the protective activity of the composition deposited on the skin. Said ester-functional polyorganosiloxanes of formula (I) can be combined with gelling or thickening compounds such as the waxes or waxy media described above.

In addition to these compounds, the sun protection compositions may include the emollients conventionally used in cosmetics, perfumes, dyes, pigments or lacquers, preservatives, active compounds against oxidation - or free radicals, skin moisturizers and water.

Said ester-functional polyorganosiloxanes of formula (I) can also be used in cosmetic make-up compositions to give them an anti-transfer property.

Anti-transfer effect makeup compositions may also contain volatile, low viscosity solvents such as isoparaffins containing 8 to 20 carbon atoms, or mixtures thereof, as well as non-volatile silicones such as cyclic or linear polydimethylsiloxanes. These makeup compositions can also contain silicone waxes, the melting point of which is at least greater than 25 ° C. The function of these waxes consists in gelling the organic phase of the composition. As examples of suitable silicone waxes, mention may be made of lauroyl trimethylolpropane siioxy silicate, risostearyltrimethylolpropane siioxy silicate, alkyl C -C3Q polydimethylsiloxanes, silicone waxes with ester function such as behenic ester dimethicone marketed by the company Rhône-Poulenc.

The makeup compositions can also contain other waxes whose melting point is generally of the order of 35 to 120 ° C. such as synthetic waxes, ceresin, paraffins, okozerite, carnauba wax, candelilla wax, cocoa butter, or a mixture thereof. The makeup compositions may also contain powders or more generally dry materials, the particle size of which is generally between 0.02 and 50 microns. These powders can be colored or not (white powder). By way of example, there may be mentioned bismuth oxychloride, mica and mica titanium, optionally functionalized silica, synthetic polymers such as Teflon, polyacrylates, polyethylenes or nylon, alumina silicate, bentonites , cellulose, magnesium derivatives such as aluminosilicate, oxide, carbonate, hydroxide, montmorillonites, talc, zinc stearate, titanium oxide, cerium oxide, or mixtures thereof . These various products may have been modified at the surface with mineral oils or silicone oils in order to improve their compatibility in hydrophobic medium.

You can also find organic or mineral pigments. The organic pigments are generally of aromatic nature such as azo, indigoid, triphenylmethane, anthraquinone, and xanthine and are included under the names D&C and FD&C. Inorganic pigments are generally insoluble metal salts of coloring additives.

Generally, the pigment / powder weight ratio is between 1/20 and 20/1 depending on the type of makeup formulation. Depending on the type of formulation, the amount of pigment will generally vary between 5 and 50% of the total composition cosmetic. Likewise, the quantity of powder may vary from approximately 10 to 20% of the weight of the composition.

The makeup composition may also contain oils, preferably mixtures of oils of different viscosity. Oils with a viscosity between 5 and 100 mPa.s can be used at 25 ° C. For example, oils such as isotridecyl isonononoate, cetyl stearate, Pisodecyl neopentanoate, coco dicaprylate / caprate, isododecanol, or mixtures thereof, may be used. It is also possible to use oils with a viscosity of between 200 and 1,000,000 mPa.s at 25 ° C. such as, for example, castor oil, lanolin derivatives, coconut oil, triglycerides, rapeseed oil, trihydroxystearin, wheat cream oil, cholesterol, or mixtures thereof. These oils can generally constitute from 1-20% of the total of the makeup formulation.

It is also possible to use other ingredients such as preservatives, antioxidants, active agents conventionally used such as vitamins or their derivatives.

The following examples are given by way of illustration.

Example 1

Hydrosilylation

Into a 5000 I reactor under nitrogen equipped with a double-jacket cooling device and a condenser, 1360 kg of allyl alcohol (i.e. approximately 23,448 moles) are introduced at ambient temperature (20-25 ° C.) and 232 g of Karstedt catalyst, Pt "0" complex in divinyltetramethylsiloxane containing 10% platinum. The reaction mass is brought to reflux of the allyl alcohol 0 ~ eb = 97 ° C.) and 2,086 kg (ie 9,676 moles of SiH units) of an oil of the following formula are introduced over 3 hours:

Me ₃ SiO (SiMe O). ₉ (SiMeHO) - ₄ SiMe ₃

The reaction is allowed to continue at 103 ° C for 4 h 30 min. The content of SiH units

.3 dosed by gasometry is less than 7.10 mole / Kg.

The volatiles are removed at atmospheric pressure for 1 hour at a temperature of 120 ° C. and then for 3 hours at a temperature of 120 ° C. under 20 mbar. Next, residual volatiles are entrained with nitrogen (2 h, 120 ° C., 40 mbar).

3642 Kg of a cloudy oil are collected. NMR and IR analyzes (v C≈O: 1745 cm ^" ) confirm the general structure of the product obtained:

Me ₃ SiO (SiMe O) _ ₉ (SiMe [CH ₂ CH2CH ₂ OH] O) -4 SiMe ₃

The number of moles of α-ethylenic units or impurities (-Si-O-allyl, free allyl alcohol) is of the order of 0.06 mole / Kg.

Esterification

3888 g (or approximately 12 moles of -OH units) of the above-prepared γ-hydroxypropylated oil are introduced into a 5000 ml reactor under nitrogen equipped with a double-jacket cooling device.

825 g (ie 10.5 moles) of acetyl chloride are introduced over 2 hours while maintaining the temperature of the reaction mass between 17 and 23 ° C.

A strong release of hydrochloric acid is observed which is eliminated by means of a stream of nitrogen. At the end of the addition, the hydrochloric acid content is 3.2% by weight. The elimination continues at room temperature (22-25 ° C) for 8 hours so as to obtain a content of 1.56% by weight. 330 g of sodium hydrogen carbonate (ie 3.9 moles) are then added and the mixture is left to react for 39 hours at room temperature (22-25 ° C.) so as to remove all the hydrochloric acid. The volatiles are removed under reduced pressure for 9 hours at 10 mbar at 100 ° C. It is then filtered on cardboard (quality 616) and 3479.4 g of a clear oil of dynamic viscosity at 25 ° C. of 44 mPa.s are collected.

NMR and IR analyzes (v C≈O: 1745 cm) confirm the general structure of the product obtained:

Me ₃ SiO (SiMe ₂ O) _ ₉ (SiMefC ^ C ^ C ^ OCOCH ^ O) ^ SiMe ₃ The number of moles of α-ethylenic units or impurities (Si-O-allyles, free allyl alcohol, allyl acetate ) is around 10 mole / Kg.

Example 2

Compatibility with organic Dhases

(10 parts by weight of the product of Example 1 per 100 parts by weight of organic phase)

Organic medium solubility / appearance * ethanol s propylene glycol s / d glycerin d hexylene glycol s

PEG-7 glyceryl cocoate d

PPG-15 stearyl ether s wheat germ oil i capryl / caprylic (Cβ-C-io) triglyceride s isopropyl myristate s mineral oil dimethicone i isodecane s / d

* The abbreviations above have the following meaning:

. s = soluble, transparent solution

. d = dispersible, cloudy

. s / d = very light touch

. i = insoluble

EXAMPLE 3 Cream Foundation

INGREDIENTS% BY WEIGHT

1. Behenic ester dimethicone 2

2. Product of Example 1 3

3. PEG-stearate (polyethylene glycol stearate) 2.5

4.isopropyl myristate 3

5. stearic acid 5

6. talc 12

7. titanium oxide 5

8. red iron oxide 0.5

9. preservative 0.2

10. Perfume 0.2

11. Deionized water qs 100 PROCEDURE

The ingredients from 1 to 4 as well as the preservative are mixed at 70 ° C and added to the water heated to 70 ° C under shearing so as to ensure emulsification. The ingredients 5 to 7 are then added with stirring and the mixture cooled to 40 ° C. The fragrance is added.

This emulsion has good properties of resistance to perspiration and of long duration.

EXAMPLE 4 Hydrating and Anti-Transfer Lipstick

INGREDIENTS% BY WEIGHT

1. Béhénic ester dimethicone 15

2. Product of Example 1 10

3. carnauba wax 2

4. ceresin 4

5. candellila wax 5

6. microcrystalline wax 2

7. beeswax 5

8. lanolin 4

9. Castor oil 20

10. hexadecyl alcohol 20

11. glycerol 3

12. glycerol monostearate 2

13. titanium oxide 2

14. Red pigment # 202 2

15. Red pigment # 4 A1 lake 3

16. Red pigment # 204 1

17. antioxidant qs

18. perfume qs

PROCEDURE

The ingredients from 1 to 8, 10, and 12 are melted under the effect of the temperature and the ingredient 11 is added with stirring. Ingredients 13 to 18 are dispersed in 9 and added to the previous mixture. Homogenization is then carried out, then the mixture is transferred to molds and cooled.

You get a lipstick with good water retention properties and comfortable to wear. EXAMPLE 5 Anti-transfer Lipstick

INGREDIENTS% BY WEIGHT synthetic wax 6 cerin 4 paraffin 3 isododecane 10 cyclomethicone 40 product of Example 1 5 behenic dimethicone ester 5 titanium oxide 3

Mica / titanium 5 bismuth oxychloride 10 Yello pigment 5 aluminum lake 3 Red pigment # 7 calcium lake 4 antioxidant qs preservative qs

Lipstick has a well-adapted sensory profile. In particular, it is easy to spread, comfortable to wear.

The anti-transfer properties are evaluated by a sensory test carried out by a group of thirty people, consisting of comparing the transfer to the skin, in comparison with a commercial formulation containing no anti-transfer agent of Example 1. After applying the lipstick on the lips and waiting for five minutes, each person proceeded to the application by kissing the upper part of their hand and judging the presence of trace of lipstick. The results are as follows:

lipstick from example 5 traditional lipstick leaves no traces 24 6 leaves traces 6 24

These results show that the lipstick containing the product of Example 1 has better anti-transfer properties than a traditional lipstick. EXAMPLE 6 Sunscreen Lotion

INGREDIENTS% BY WEIGHT product of Example 1 10 cyclomethicone 10

Parsol MCX 5 isopropyl myristate 5 oleth-25 2 ceteth-20 1 potassium lauryl phosphate 2 glycerol 3 deionized water 62

This emulsion sunscreen has good spreading properties on the skin and resistance to water.

EXAMPLE 7 Antiperspirant / Deodorant

INGREDIENTS% BY WEIGHT

1. Cyclomethicone 7

2. Dimethicone copolyol 5

3. product of example 1 7

4. aluminum hydrochloride 50

5.propylene glycol 15

6.water 16

A mixture of ingredients 3, 4 and 5 is slowly added with vigorous stirring to a mixture of ingredients 1 and 2. The resulting dispersion is homogenized. A transparent gel is obtained after adjustment of the refractive indices. This formulation has good resistance to perspiration.

Example 8: "Roll-on" (deodorant)

INGREDIENTS% BY WEIGHT product of Example 1 5 cyclomethicone 70

Anhydrous ethanol 5 aluminum zirconium tetrachlorohydrex GLY 20 EXAMPLE 9 Hair Spray

INGREDIENTS% BY WEIGHT

Cyclomethicone 85 cyclomethicone (and) diphenyidimethicone 10 product of example 1 5

EXAMPLE 10 Treatment Formulation for Cuticle

INGREDIENTS% BY WEIGHT Cyclomethicone 85 cyclomethicone (and) dimethicone 10 product of Example 1 5

EXAMPLE 11 Cleansing Milk

INGREDIENTS INCI name% in poi

PHASE A

Paramul J Cetearyl Alcohol and Ceteareth-20 2.00

Dermol DISD diisostearyl dimer Dilinoleate 4.00

Waglinol 6016 isopropyl palmitate 7.00 camellia oil Camellia Kissi oil 4.00

Alcohol 260 Ethanol 1, 00

PHASE B distilled water Aqua 73.70

Rhodicare S Xanthan gum 1, 00

PHASE C

Miranol C2M conc NP disodium cocoamphodiacetate 2.00

PHASE D

Product of Example 1 5.00

PHASE E

Perfume FBF 0239 Fragrance 0.30

Acid citric 50% Citric Acid DH 6.2 PROCEDURE

Heat phase A to 75 ° C. Disperse Rhodicare S in water and heat to 75 ° C. As soon as the two phases are homogeneous, emulsify phase A in phase B. L. straighten cool down to 40 ° C and add phases C and D. Finally add phase E as soon as it returns to room temperature.

CHARACTERISTICS pH: 6.20

EXAMPLE 12 Makeup Removing Lotion

INGREDIENTS INCI name% by weight

PHASE A distilled water Aqua 84.20 Jaguar C 162 hydroxypropyl guar hydroxypropyl 0.50 trimonium chloride

Methyl parahydroxybenzoate methyl paraben 0.20

PHASE B

Product of Example 1 10.00

Glycerol Glycerin 5.00

PHASE C extract of Senega Polygala Senega extract 0.10

PROCEDURE

Incorporate the Jaguar in PHASE A. When obtaining transparency, incorporate phases B and C.

CHARACTERISTICS Transparent product pH: 6.20 Example 13: After Sun Cream

INGREDIENTS name INCI name% by weight

PHASE A product of Example 1 5.0

MIRASIL C-DPDM Cyclomethicone (and) 5.0 Diphenyidimethicone

Octyl Cocoate Octyl Cocoate 7.0

Jojoba Oil Jojoba (Buxus Chinensis) Oil 2.0

Grape seed oil Grater (Vitis Vinifera) Seed Oil 1, 0

PHASE B

TEFOSE 63 PEG-6 (and) PEG-32 (and) Glycol 10.0 Stearate

Aliantoine Allantoin 0.5 deionized water Aqua qs 100

PHASE C preservative Preservative q.s.

PHASE D perfume Perfume q.s.

Heat phases A and B separately at 75 ° C. Homogenize phase A, add it to phase B under low shear. Cool to 45 ° C, add phases C and D and stir until cooling to room temperature.

CHARACTERISTICS

White cream appearance

PH: 6.5

Viscosity at 25 ° C: 70,000 mPa.s (Brookfield: Helipath stand, spindle

C, 10 rpm) Example 14: Sun Oil

INGREDIENTS INCI name% by weight

Cyclomethicone Cyclomethicone 27.0

Isopropyl Palmitate Isopropyl Palmitate 25.0

Diisopropyl Adipate Diisopropyl Adipate 25.0 product of Example 1 5.0

MIRASIL C-DPDM Cyclomethicone (and) 15.0 Diphenyidimethicone

Benzophenone-3 Benzophenone-3 3.0

Dye q.s dye

PROCEDURE

Dissolve Benzophenone-3 in the esters with stirring. Add the product (IV) and homogenize. Add the MIRASIL C-DPDM, and homogenize.

CHARACTERISTICS

Appearance: transparent liquid

Viscosity at 25 ° C: 60mPa.s (Brookfield: spindle n ° 2, 100 rpm)

EXAMPLE 15 Sun Gel

INGREDIENTS name CTFA% by weight

PHASE A

Myritol 318 Caprylic / Capric Triglyceride 17.5

Cetiol V Decyl oleate 7.8 product from Example 1 4.0

Mirasil DPDM Diphenyl Dimethicone 5.8

Vaseline Oil Paraffin Oil 50.8

PHASE B

Rhodialux A Benzophenone 3 2.7

PHASE C

Novogel ST Aluminum Stearate (and) Ore Oil 7.8

Isostearic acid Isostearic Acid 3.6 PROCEDURE

- Successively mix the compounds of phase A

- Add Rhodialux A to the previous mixture and homogenize in a water bath at 75 ° C - Add Novogel ST and isostearic acid and stir at 75 ° C until complete homogenization

- Cool with stirring

CHARACTERISTICS Appearance: translucent gel

Example 16: Make-up Remover

INGREDIENTS INCI name% by weight

PHASE A

Hetester PHA Propylene Glycol lsoceteth-3 acetate 10.00 product of Example 1 5.00

MIRASIL CM5 cyclomethicone 5.00

Dermol M5 Caprylic / Capric Triglycerides 5.00

PHASE B

Deionized water Aqua qsp 100

RHODICARE S Xanthan gum 0.80

PHASE C

MIRANOL ULTRA C32 Sodium Cocoamphoacetate 2.00

PHASE D

Perfume Perfume 0.20

PROCEDURE Disperse RHODICARE S in water, add water, then phase A in phase B with vigorous stirring. Add phase C and phase D. Adjust the pH with citric acid. CHARACTERISTICS

White liquid appearance

PH: 6.0-6.5

Viscosity at 25 ° C: 3000 mPa.s (Brookfield sp4, 20 rpm)

Example 17: Light makeup

INGREDIENTS name CTFA% by weight

PHASE A

RHODICARE H Xanthan gum 1, 00

Propylene glycol Propylene glycol 5.00

Magnesium Aluminum Silicate Magnesium Aluminum Silicate 0.50

Aqua water qs 100

PHASE B

Cetyl acetate (and) Acetylated lanolin Cetyl acetate (and) Acetylated lanolin 2.00 alcohol alcohol product of Example 1 4.00

C12-C15 Alkyl benzoate C12-C15 Alkyl benzoate 5.00

Isopropyl myristate Isopropyl myristate 5.00

Phenoxyethanol Phenoxyethanol 0.50

Glyceryl stearate (and) PEG-100 Glyceryl stearate (and) PEG-100 5.00 stearate stearate

PHASE C titanium dioxide and iron oxides Titanium dioxide and Iron oxides 9.50

PROCEDURE

Disperse the Magnesium Aluminum Silicate and RHODICARE H in water with vigorous stirring and heat to 75 ° C. Mix phase B and heat to 75 ° C.

Add phase C to phase B and mix until a homogeneous mixture is obtained.

Add the mixture of phases B and C to phase A with vigorous stirring.

Cool to room temperature and add the fragrance. CHARACTERISTICS

PH 5.0-6.0

Viscosity at 25 ° C 11000 mPa.s (Brookfield n ° 4, 5 rpm)

Example 18: Day cream

INGREDIENTS name CTFA% by weight

PHASE A paraffin oil Ore Oil 5.0

Migiyol 812 N Caprylic / Capric Triglyceride 5.0

Isopropyl myristate Isopropyl Myristate 3.0 sunflower oil Sunflower Seed Oil 4.0 product of Example 1 0.5

Lorol C18 Stearyl Alcohol 1, 0 α -Tocopherolacetate Tocopheryl acetate 2.0

PHASE B MIRASOFT POH Hydrogenated Palm Oil 5.0

Sucroglyceride glycerol Glycerin 3.0 preservative preservative q.s. deionized water Aqua qsp 100 RHODICARE S Xanthan Gum 0.2

PROCEDURE

Heat the two phases to 75 ° C. Add phase A to phase B under high shear. Homogenize with Ultra Turrax and cool to temperature with stirring.

CHARACTERISTICS

White cream appearance

PH: 6-7

Viscosity at 25 ° C: 32,800 mPa.s Brookfield LVT, spindle E, 6 rpm Example 19: Night cream

CTFA INGREDIENTS% by weight

PHASE A

Paraffin oil Ore Oil 15.0

Arlamol HD Isohexadecane 10.0

Miglyol 812 N Caprylic / Capric Triglyceride 5.0

Wheat Germ Oil 3.0 Wheat Germ Oil Product of Example 1 0.5

Arlacel 60 Sorbitane Stearate 2.0

Lorol C18 Stearyl Alcohol 0,5 a -Tocopherolacetat Tocopheryl Acetate 1, 0

PHASE B

MIRASOFT POH Hydrogenated Palm Oil 5.0 Sucroglyceride

Glycerin Glycerin 4.0

Preservative Preservative q.s.

RHODICARE S Xanthan Gum 0.3

Aqua water qs 100

PROCEDURE

CHARACTERISTICS

White cream appearance

PH: 6-7

Viscosity at 25 ° C: 100600mPa.s (Brookfield LVT, spindle F, 6 rpm) Example 20: Solar emulsion (oil in water) of SPF equal to 10

INCI INGREDIENTS name% by weight

PHASE A

Arlatone 985 POE-5-Stearyl Stearate 4.0

Brij 721 Steareth-21 2.0

Parsol MCX Octyl Methoxycinnamate 5.0 product of Example 1 4.0

DUB DNPG Neopentyl Diheptanoate 4.0

Dermol M5 Caprylic / Capric Triglycerides 3.0

Grape Grapeseed Oil (Vitis Vinifera) Seed Oil 3.0

MIRASIL WAX B Behenic Ester Dimethicone 1, 0

Oxynex 2004 BHT (and) Glyceryl Stearate (and) 0.1 Glyceryl Oleate (and) Ascorbyl Palmitate (and) Citric Acid (and) Propylene Glycol

PHASE B Aqua deionized water qsp 100 Atlas G2330 Sorbeth-30 4,0 Preservative qs Perfume Perfume qs

PROCEDURE

Heat phases A and B to 75 ° C separately. Under very high shear, incorporate phase A into phase B and homogenize. Cool to room temperature under low shear and add preservative and fragrance.

CHARACTERISTICS

White cream appearance

PH: 6 EXAMPLE 21 Base for Cream

INGREDIENTS INCI name% by weight

PHASE A

Mirasil DM300 Dimethicone 15.0 product of Example 1 5.0

PHASE B

Rhodicare S Xanthan Gum 0.15

Arlatone 2121 Sorbitan Stearate (and) Sucrose Cocoate 5.5

Glycerol Glycerin 4.0

Preservative Preservative qs

Aqua water qs 100

PROCEDURE

Disperse and hydrate Rhodicare S in water. Add the glycerol and Arlatone 2121. Heat phases A and B separately to 75 ° C. Add phase A to phase B with vigorous stirring and homogenize for one minute. Cool to room temperature under low shear and add the preservative and fragrance.

CHARACTERISTICS

PH: 6

Viscosity at 25 ° C: 78,000 mPa.s (Brookfield LVT, sp E, 1,5 rpm)

Example 22: Deodorant - transparent gel

INGREDIENTS INCI name% by weight

Mirasil PTM Phenyl trimethicone 5.3

Product of Example 1 4.0

Triclosan Triclosan 0.3

PPG-3 Myristyl ether PPG-3 Myristyl ether 67.6

Propanediol-1,2 Propanediol-1, 2 15.7

Na stearate C7L Sodium stearate 6.0

Perfume Perfume q.s.

Dye GREEN 7000 Dye 0.1 PROCEDURE

Dissolve the Triclosan in propanediol-1, 2, add the PPG-3 myristyl ether, and the silicones at 30 ° C, with stirring. Add the sodium stearate and stir until dissolved. Heat to 60 ° C, add the perfume and the dye. After cooling, a translucent gel is obtained.

EXAMPLE 23 Body Lotion

INGREDIENTS INCI name% by weight

PHASE A

Product of Example 1 2.0 MIRASIL DM 100 Dimethicone 3.0 Isopropyl Palmitate Isopropyl Palmitate 3.0 Tefose 2561 PEG-6 Stearate (and) Ceteth-20 (and) 7.0

Glyceryl Stearate (and) Steareth-20

PHASE B Rhodicare S Xanthan Gum 0.3 Preservative Preservative q.s Water Aqua qs 100

PROCEDURE

Prepare the xanthan gum solution and heat to 75 ° C. Heat the fatty phase to

75 ° C. Add phase B to phase A with stirring.

CHARACTERISTICS

Appearance White fluid lotion

PH: 6.5-7.0

Claims

1) Use as anti-transfer agents, in cosmetic compositions, of polyorganosiloxanes with ester functions of formula (I) below:

R ¹ R ² R ³ Si O (R ⁴ R ⁵ Si O) _p (R ⁶ Q Si O) _q Si R ³ R ² R ¹ (I) where:

- the symbols R ¹ , R ² are identical or different and represent

. a C- alkyl radical | to Cg or phenyl, preferably methyl. or a group -OR ⁷ , where R ⁷ represents a linear or branched C- alkyl radical | to Cg, preferably methyl

the symbols R ⁴ and R 6 are identical or different and represent a C 1 -C 6 alkyl or phenyl radical, preferably methyl,

- the identical or different symbols R ³ represent. a linear or branched C- alkyl radical | with Cg or phenyl, preferably methyl

. the Q symbol

. or a group -OR ⁷ , where R ⁷ represents a linear or branched C- alkyl radical | to C4, preferably methyl - the identical or different symbols Q, represent an ester function or an alcohol function, of formulas (1) and (2) respectively:

- R'OCOR "(1) -R'OH (2) where:

. R 'represents a linear alkylene group or branched C 3 - C ₂ _o> preferably C3 - Cj _2, especially trimethylene or 2-methyltrimethylene,. R "represents the methyl group, at least one of the symbols Q representing an ester function of formula (1)

2) Process for providing anti-transfer properties to cosmetic compositions by adding to said compositions at least one polyorganosiloxane containing ester functions of formula (I) below: R1 R ² R ³ Si O (R ⁴ R ⁵ Si O) _p (R ^ Q Si O) _q Si R ³ R ² R ¹ (I) where:

- the symbols R ¹ , R ² are identical or different and represent

. a C1-C6 alkyl or phenyl radical, preferably methyl. or a group -OR ⁷ , in which R ⁷ represents a linear or branched C 1 to C 8 alkyl radical, preferably methyl

the symbols R ⁴ , R ^ and R> are identical or different and represent an alkyl radical in Cj to Cg or phenyl, preferably methyl,

. the Q symbol

- R'OCOR "(1) -R'OH (2) where:

. R 'represents a linear alkylene group or branched C 3 - C ₂ Q, preferably C3 - Cj _2, especially trimethylene or 2-methyltrimethylene,. R "represents the methyl group, at least one of the symbols Q representing an ester function of formula (1)

3) Use according to claim 1) or method according to claim 2), characterized (e) in that said polyorganosiloxanes with ester functions are chosen from those with acetoxyalkyl functions of formulas (II), (III) and (IV) below, (II) very particularly Me ₃ Si O (SiMe ₂ O) _p . (SiMeQO) _q > SiMe3 (II)

Me ₂ Q Si O (SiMe O) _p - (SiMeQO) _q . If Q Me (III)

Me ₂ Q Si O (SiMe O) _p - Si Q Me ₂ (IV) formulas in which:

. Me represents the methyl radical

. Q. represents an average number in the range of 0 to 500, preferably in the range of 5 to

100

. a represents an average number of the order of 1 to 50, preferably of the order of 1 to

30

. Q represents an acetoxyalkyl function of formula - ROCOCH3 or an alcohol function -R'OH, where R 'represents a trimethylene or 2-methyltrimethylene group, very particularly trimethylene, at least one of the symbols Q representing an acetoxyalkyl function - ROCOCH3.

4) Use according to claim 1) or 3), or method according to claim 2) or 3), characterized (e) in that all the symbols Q represent an ester function.

5) Use according to claim 1), 3) or 4), or process according to any one of claims 2) to 4), characterized (e) in that said polyorganosiloxanes having ester functions have overall contents of siloxane units a olefinic and / or olefinic α impurities corresponding to a number of olefinic groups per 100 g of polyorganosiloxane having an ester function of less than 10 " ³ , preferably less than 5x10" ⁴ .

6) Use according to any one of claims 1) and 3) to 5), or method according to any one of claims 2) to 5), characterized (e) in that said polyorganosiloxanes containing ester functions are liquid state at a temperature of the order of 10 to 30 ° C under atmospheric pressure and have viscosities of less than 5000 mPa.s.

7) Use according to any one of claims 1) and 3) to 6), or process according to any one of claims 2) to 6), characterized (e) in that said polyorganosiloxanes having ester functions are used in an amount of 0.1% to 30%, preferably from 3% to 10% of the weight of said cosmetic compositions.

8) Cosmetic compositions comprising at least one polyorganosiloxane containing ester functions of formula (I), the use of which is the subject of any one of claims 1) and 3) to 6). 9) Cosmetic compositions according to claim 8) characterized in that said polyorganosiloxanes having ester functions are present in an amount of 0.1% to 30%, preferably from 3% to 10% by weight of said compositions.

10) Use according to any one of claims 1) and 3) to 7), method according to any one of claims 2) to 7), or cosmetic compositions according to claim 8) or 9), characterized (e) ( es) in that said compositions further comprise at least one vehicle compatible with the hair and / or the skin.

11) Use, process or cosmetic compositions according to claim 10), characterized (eXes) in that said vehicle is water, an alcoholic solvent, a volatile silicone or their mixtures.

12) Use, process or cosmetic compositions according to claim 11), characterized (eXes) in that said vehicle is an alcoholic solvent representing at least 3%, preferably from 5 to 90% by weight of said compositions.

13) Use according to any one of claims 1), 3) to 7), 10) to 12), method according to any one of claims 2) to 7), 10) to 12), or cosmetic compositions according to claim 8) to 12), characterized in that said cosmetic compositions also comprise at least 0.5% by weight of at least one cosmetically acceptable ingredient.

14) Use, process or cosmetic compositions according to claim 13), characterized (e) (es) in that said cosmetically acceptable agent is a surfactant, a non-volatile silicone, a conditioning agent, a fixing resin, a functional polymer protective, a plasticizing agent, a metal sequestering agent, a humectant, a water-soluble or water-dispersible polymer, a silicone wax, an oily medium, a thickening, gelling or solidifying agent, a texture agent, an astringent agent, a bactericidal agent or bacteriostatic, an emollient agent, a mineral or organic anti UV agent, a pigment, an antioxidant.

15) Use, process or cosmetic compositions according to claim 13) or 14), characterized (e) (es) in that said compositions comprise - from 1 to 60% by weight, preferably from 5 to 25% by weight, d '' at least one surfactant

- from 0.5 to 50% by weight, preferably from 0.5 to 10% by weight, of at least one polyorganosiloxane containing ester functions of formula (I), (II), (III) or (IV). 16) Use according to any one of Claims 1), 3) to 7), and 10) to 15), method according to any one of Claims 2) to 7), and 10) to 15), or cosmetic compositions according to claim 8) to 15), characterized (e) (es) in that said compositions mainly comprise an oily medium which may be thickened.

17) Use, process or cosmetic compositions according to claim 16), characterized (e) (es) in that the quantity of polyorganosiloxane containing ester functions of formula (I), (II), (III) or (IV) work is from 0.2 to 50, preferably from 2 to 10 parts by weight per 100 part by weight of said oily medium.

18) Use according to any one of claims 1), 3) to 7), and 10) to 17), method according to any one of claims 2) to 7), and 10) to 17), or cosmetic compositions according to claim 8) to 17), characterized (e) (es) in that said cosmetic compositions are in the form of sun gels, deodorants, antiperspirants, make-up or care products.